CH691536A5 - Verfahren zur Herstellung von reinem Citalopram - Google Patents

Verfahren zur Herstellung von reinem Citalopram Download PDF

Info

Publication number: CH691536A5
Authority: CH; Switzerland
Prior art keywords: cyanide; citalopram; reaction; film distillation; carried out
Prior art date: 2000-12-28

Application number

CH00546/01A

Other languages

German (de)

English (en)

Inventor

Federico Sbrogio

Andrea Castellin

Giulio Volpe

Original Assignee

Lundbeck & Co As H

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-28

Filing date

2001-03-22

Publication date

2001-08-15

2001-03-22 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2001-07-26 Priority to CH01412/01A priority Critical patent/CH691999A5/de

2001-08-15 Publication of CH691536A5 publication Critical patent/CH691536A5/de

Links

WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title claims description 41
229960001653 citalopram Drugs 0.000 title claims description 41
238000004519 manufacturing process Methods 0.000 title description 4
238000000034 method Methods 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 30
238000004821 distillation Methods 0.000 claims description 30
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000010409 thin film Substances 0.000 claims description 13
239000010408 film Substances 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
238000000746 purification Methods 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000002585 base Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000002825 nitriles Chemical group 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 5
-1 5-thiazolinyl group Chemical group 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
229940005513 antidepressants Drugs 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 3
239000003826 tablet Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
GHZPDRVHYHFILK-UHFFFAOYSA-N 3-chloro-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Cl)OC(=O)C2=C1 GHZPDRVHYHFILK-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000013542 high molecular weight contaminant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH00546/01A 2000-12-28 2001-03-22 Verfahren zur Herstellung von reinem Citalopram CH691536A5 (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH01412/01A CH691999A5 (de)	2000-12-28	2001-07-26	Verfahren zur Herstellung von reinem Citalopram.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DKPA200001943		2000-12-28

Publications (1)

Publication Number	Publication Date
CH691536A5 true CH691536A5 (de)	2001-08-15

Family

ID=8159933

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH00546/01A CH691536A5 (de)	2000-12-28	2001-03-22	Verfahren zur Herstellung von reinem Citalopram

Country Status (41)

Country	Link
US (2)	US6855834B2 (es)
EP (1)	EP1181272B1 (es)
JP (1)	JP2003519121A (es)
KR (1)	KR100430746B1 (es)
CN (1)	CN1366526A (es)
AR (1)	AR029898A1 (es)
AT (2)	ATE222899T1 (es)
AU (3)	AU3920201A (es)
BE (2)	BE1013417A6 (es)
BG (1)	BG106219A (es)
BR (1)	BR0106271A (es)
CA (1)	CA2359810C (es)
CH (1)	CH691536A5 (es)
CZ (1)	CZ293140B6 (es)
DE (1)	DE60100016T2 (es)
DK (1)	DK1181272T3 (es)
EA (1)	EA003459B1 (es)
ES (2)	ES2181663T3 (es)
FI (2)	FI108640B (es)
FR (1)	FR2818977B1 (es)
GB (2)	GB2356199B (es)
GR (1)	GR20010100131A (es)
HK (1)	HK1049332A1 (es)
HR (1)	HRP20020005A2 (es)
HU (2)	HU0101028D0 (es)
IE (2)	IES20010253A2 (es)
IL (1)	IL147162A0 (es)
IS (1)	IS5884A (es)
IT (1)	ITMI20010604A1 (es)
MX (1)	MXPA01013336A (es)
NL (1)	NL1017534C1 (es)
NO (1)	NO313047B1 (es)
NZ (1)	NZ516299A (es)
PL (1)	PL353369A1 (es)
PT (1)	PT1181272E (es)
SE (1)	SE0103044L (es)
SK (1)	SK284418B6 (es)
TR (1)	TR200200018T1 (es)
UA (1)	UA71635C2 (es)
WO (1)	WO2001047877A2 (es)
ZA (1)	ZA200110133B (es)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR022329A1 (es)	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
AU759716B2 (en)	1999-04-14	2003-04-17	H. Lundbeck A/S	Method for the preparation of citalopram
ITMI991579A1 (it)	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
ITMI991581A1 (it) *	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
EP1228056B1 (en)	1999-10-25	2004-09-22	H. Lundbeck A/S	Method for the preparation of citalopram
DE69920526T2 (de)	1999-10-25	2006-02-23	H. Lundbeck A/S	Verfahren zur herstellung von citalopram
AR026063A1 (es)	1999-11-01	2002-12-26	Lundbeck & Co As H	Metodo para la preparacion de 5-carboxiftalida.
PT1246812E (pt)	1999-12-28	2004-08-31	Lundbeck & Co As H	Metodo para a preparacao de citalopram
UA73336C2 (en)	1999-12-30	2005-07-15	Lundbeck & Co As H	A method for the preparation of 5-cyano-phtalid
ES2206177T3 (es)	2000-01-14	2004-05-16	H. Lundbeck A/S	Metodo para la preparacion de 5-cianoftalida.
IES20010157A2 (en)	2000-03-03	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
NL1017500C1 (nl)	2000-03-13	2001-04-26	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
IL151490A0 (en)	2000-03-13	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
WO2001068629A1 (en)	2000-03-13	2001-09-20	H. Lundbeck A/S	Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
DE60101786T2 (de)	2000-03-14	2004-07-15	H. Lundbeck A/S, Valby	Verfahren zur herstellung von citalopram
PL360115A1 (en) *	2000-03-16	2004-09-06	H.Lundbeck A/S	Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
AR032455A1 (es)	2000-05-12	2003-11-12	Lundbeck & Co As H	Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
IL144816A (en)	2000-08-18	2005-09-25	Lundbeck & Co As H	Method for the preparation of citalopram
IL147226A (en)	2000-12-22	2006-04-10	Lundbeck & Co As H	Process for the preparation of pure citalopram
PL353369A1 (en)	2000-12-28	2003-11-17	H.Lundbeck A/S	Process for the preparation of pure citalopram
GB2376945A (en) *	2001-06-27	2002-12-31	Cipla Ltd	Citalopram preparation
US7148364B2 (en)	2002-01-07	2006-12-12	Sun Pharmaceutical Industries	Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile
ES2194597B2 (es) *	2002-01-25	2004-08-01	Esteve Quimica, S.A.	Procedimiento para la obtencion de citalopram.
GB2386119A (en) *	2002-02-27	2003-09-10	Cipla Ltd	Purification of citalopram
GB0204607D0 (en) *	2002-02-27	2002-04-10	Matrix Lab Ltd	Process
EP1346989A1 (en) *	2002-03-21	2003-09-24	Jubilant Organosys Limited	Improved process for the preparation of citalopram and its hydrobromide
AU2003223105A1 (en) *	2003-03-24	2004-10-18	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
EP1486492A3 (en) *	2003-06-10	2005-02-23	Sun Pharmaceuticals Industries Ltd.	A process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran.
CN100569765C (zh)	2003-12-19	2009-12-16	杭州民生药业集团有限公司	西酞普兰中间体晶体碱
TWI347942B (en) *	2005-06-22	2011-09-01	Lundbeck & Co As H	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
US7834201B2 (en)	2005-06-22	2010-11-16	H. Lundbeck A/S	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base

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NL135959C (es)	1964-12-23
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2001
- 2001-03-07 PL PL01353369A patent/PL353369A1/xx not_active Application Discontinuation
- 2001-03-07 EP EP01913727A patent/EP1181272B1/en not_active Expired - Lifetime
- 2001-03-07 CN CN01801127A patent/CN1366526A/zh active Pending
- 2001-03-07 HK HK03101406.3A patent/HK1049332A1/zh unknown
- 2001-03-07 TR TR2002/00018T patent/TR200200018T1/xx unknown
- 2001-03-07 SK SK1847-2001A patent/SK284418B6/sk unknown
- 2001-03-07 AU AU39202/01A patent/AU3920201A/en active Pending
- 2001-03-07 EA EA200200016A patent/EA003459B1/ru not_active IP Right Cessation
- 2001-03-07 CA CA002359810A patent/CA2359810C/en not_active Expired - Fee Related
- 2001-03-07 IL IL14716201A patent/IL147162A0/xx unknown
- 2001-03-07 DK DK01913727T patent/DK1181272T3/da active
- 2001-03-07 BR BR0106271-9A patent/BR0106271A/pt not_active IP Right Cessation
- 2001-03-07 JP JP2001549350A patent/JP2003519121A/ja active Pending
- 2001-03-07 PT PT01913727T patent/PT1181272E/pt unknown
- 2001-03-07 MX MXPA01013336A patent/MXPA01013336A/es active IP Right Grant
- 2001-03-07 DE DE60100016T patent/DE60100016T2/de not_active Expired - Fee Related
- 2001-03-07 AT AT01913727T patent/ATE222899T1/de not_active IP Right Cessation
- 2001-03-07 KR KR10-2001-7016757A patent/KR100430746B1/ko not_active Expired - Fee Related
- 2001-03-07 WO PCT/DK2001/000148 patent/WO2001047877A2/en not_active Ceased
- 2001-03-07 ES ES01913727T patent/ES2181663T3/es not_active Expired - Lifetime
- 2001-03-07 AU AU2001100399A patent/AU2001100399B4/en not_active Ceased
- 2001-03-07 HR HR20020005A patent/HRP20020005A2/hr not_active Application Discontinuation
- 2001-03-08 NL NL1017534A patent/NL1017534C1/nl not_active IP Right Cessation
- 2001-03-09 HU HU0101028A patent/HU0101028D0/hu unknown
- 2001-03-09 IS IS5884A patent/IS5884A/is unknown
- 2001-03-12 CZ CZ2001891A patent/CZ293140B6/cs not_active IP Right Cessation
- 2001-03-12 GB GB0105981A patent/GB2356199B/en not_active Revoked
- 2001-03-13 FI FI20010501A patent/FI108640B/fi active
- 2001-03-13 NO NO20011272A patent/NO313047B1/no unknown
- 2001-03-15 IE IE20010253A patent/IES20010253A2/en not_active IP Right Cessation
- 2001-03-15 AR ARP010101210A patent/AR029898A1/es unknown
- 2001-03-16 GR GR20010100131A patent/GR20010100131A/el unknown
- 2001-03-21 AT AT0020901U patent/AT4368U1/de unknown
- 2001-03-22 BE BE2001/0189A patent/BE1013417A6/fr not_active IP Right Cessation
- 2001-03-22 IT IT2001MI000604A patent/ITMI20010604A1/it unknown
- 2001-03-22 CH CH00546/01A patent/CH691536A5/de not_active IP Right Cessation
- 2001-03-26 FR FR0104025A patent/FR2818977B1/fr not_active Expired - Fee Related
- 2001-07-03 UA UA2002021553A patent/UA71635C2/uk unknown
- 2001-07-05 HU HU0102818A patent/HUP0102818A3/hu unknown
- 2001-07-05 IE IE20010632A patent/IES20010632A2/en not_active IP Right Cessation
- 2001-07-09 BE BE2001/0466A patent/BE1013316A6/fr not_active IP Right Cessation
- 2001-07-13 GB GB0117095A patent/GB2361697A/en not_active Withdrawn
- 2001-07-26 FI FI20011578A patent/FI20011578A0/fi not_active IP Right Cessation
- 2001-07-27 ES ES200101763A patent/ES2170733B1/es not_active Expired - Lifetime
- 2001-08-27 AU AU65478/01A patent/AU750006B1/en not_active Ceased
- 2001-09-14 SE SE0103044A patent/SE0103044L/xx not_active Application Discontinuation
- 2001-12-10 ZA ZA200110133A patent/ZA200110133B/en unknown
- 2001-12-13 BG BG106219A patent/BG106219A/xx unknown
- 2001-12-20 NZ NZ516299A patent/NZ516299A/xx unknown
- 2001-12-20 US US10/035,005 patent/US6855834B2/en not_active Expired - Fee Related
2003
- 2003-02-10 US US10/361,800 patent/US20030178295A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CN1366526A (zh)	2002-08-28
HRP20020005A2 (en)	2003-04-30
AR029898A1 (es)	2003-07-23
IES20010253A2 (en)	2002-03-06
FI20011578A0 (fi)	2001-07-26
EA200200016A1 (ru)	2002-04-25
FR2818977A1 (fr)	2002-07-05
EP1181272B1 (en)	2002-08-28
NO313047B1 (no)	2002-08-05
GB0117095D0 (en)	2001-09-05
BE1013417A6 (fr)	2001-12-04
KR20020073379A (ko)	2002-09-26
HUP0102818A2 (hu)	2001-12-28
PL353369A1 (en)	2003-11-17
EP1181272A2 (en)	2002-02-27
HK1049332A1 (zh)	2003-05-09
NO20011272D0 (no)	2001-03-13
UA71635C2 (uk)	2004-12-15
FI20010501A0 (fi)	2001-03-13
GB2356199A (en)	2001-05-16
ES2170733B1 (es)	2003-12-16
ATE222899T1 (de)	2002-09-15
NO20011272L (no)	2002-07-01
IES20010632A2 (en)	2002-03-06
AT4368U1 (de)	2001-06-25
BE1013316A6 (fr)	2001-11-06
ITMI20010604A1 (it)	2002-09-22
HUP0102818A3 (en)	2003-07-28
JP2003519121A (ja)	2003-06-17
US6855834B2 (en)	2005-02-15
NL1017534C1 (nl)	2001-04-26
GB0105981D0 (en)	2001-05-02
NZ516299A (en)	2002-12-20
BG106219A (en)	2002-08-30
FR2818977B1 (fr)	2003-12-05
HU0101028D0 (en)	2001-05-28
AU3920201A (en)	2001-07-09
US20030178295A1 (en)	2003-09-25
ES2170733A1 (es)	2002-08-01
WO2001047877A3 (en)	2001-12-27
ITMI20010604A0 (it)	2001-03-22
CZ2001891A3 (cs)	2002-08-14
ES2181663T3 (es)	2003-03-01
CA2359810C (en)	2002-11-05
SK18472001A3 (sk)	2002-05-09
US20020087012A1 (en)	2002-07-04
MXPA01013336A (es)	2002-07-09
GB2361697A (en)	2001-10-31
SK284418B6 (sk)	2005-04-01
CA2359810A1 (en)	2001-07-05
WO2001047877A2 (en)	2001-07-05
KR100430746B1 (ko)	2004-05-10
DE60100016T2 (de)	2003-04-17
HU0102818D0 (en)	2001-09-28
FI108640B (fi)	2002-02-28
ZA200110133B (en)	2003-01-13
CZ293140B6 (cs)	2004-02-18
AU2001100399B4 (en)	2002-03-21
AU2001100399A4 (en)	2001-11-01
IS5884A (is)	2002-06-28
DE60100016D1 (de)	2002-10-02
AU750006B1 (en)	2002-07-11
GB2356199B (en)	2001-10-03
DK1181272T3 (da)	2002-12-30
TR200200018T1 (tr)	2002-06-21
BR0106271A (pt)	2002-05-21
SE0103044L (sv)	2002-06-29
EA003459B1 (ru)	2003-06-26
SE0103044D0 (sv)	2001-09-14
PT1181272E (pt)	2003-01-31
IL147162A0 (en)	2002-08-14
GR20010100131A (el)	2002-10-09

Publication	Publication Date	Title
DE60100016T2 (de)	2003-04-17	Verfahren zur herstellung von reinem citalopram
AT409961B (de)	2002-12-27	Verfahren zur herstellung von citalopram
DE60100022T3 (de)	2011-11-17	Verfahren zur herstellung von citalopram-salzen
DE10112829C1 (de)	2002-07-25	Verfahren zur Herstellung von gereinigtem Citalopram
DE69907037T3 (de)	2010-02-18	Verfahren zur herstellung von citalopram
AT409960B (de)	2002-12-27	Verfahren zur herstellung von citalopram
DE69801764T2 (de)	2002-07-04	Verfahren zur herstellung von citalopram
DE69719098T2 (de)	2004-02-12	Verfahren zur herstellung von citalopram
CH692421A5 (de)	2002-06-14	Verfahren zur Herstellung von Citalopram.
DE60133280T2 (de)	2009-04-16	Verfahren zur herstellung von citalopram
DE69920526T2 (de)	2006-02-23	Verfahren zur herstellung von citalopram
DE10112828C1 (de)	2002-11-21	Verfahren zur Herstellung von Citalopram
DE10164725B4 (de)	2004-08-26	Verfahren zur Herstellung von gereinigtem Citalopram
CH691999A5 (de)	2001-12-31	Verfahren zur Herstellung von reinem Citalopram.
AT4682U1 (de)	2001-10-25	Verfahren zur herstellung von reinem citalopram
AT4681U1 (de)	2001-10-25	Verfahren zur herstellung von reinem citalopram
CH691998A5 (de)	2001-12-31	Verfahren zur Herstellung von reinem Citalopram.

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2008-10-31	PL	Patent ceased

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2007-10-30

PFA

Name/firm changed

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Free format text: H. LUNDBECK A/S#7-9 OTTILIAVEJ#DK-2500 KOPENHAGEN-VALBY (DK) -TRANSFER TO- H. LUNDBECK A/S#7-9 OTTILIAVEJ#DK-2500 KOPENHAGEN-VALBY (DK)

2008-10-31

Patent ceased